2-Furancarboxylic acid, hydrazide → N'-(2-amino-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide

HRID 2239805Notes

Reaction equation

HRID 2239805 reaction equation
Cl[C:2]1[C:3]2[CH:11]=[CH:10][NH:9][C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1.[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([NH:19][NH2:20])=[O:18]>C(O)CCC>[NH2:8][C:6]1[N:7]=[C:2]([NH:20][NH:19][C:17]([C:13]2[O:12][CH:16]=[CH:15][CH:14]=2)=[O:18])[C:3]2[CH:11]=[CH:10][NH:9][C:4]=2[N:5]=1

Participants

4

Reactant 2

HCID 187312-Furancarboxylic acid, hydrazideHCID 53244134-chloro-7H-pyrrolo(2,3-d)pyrimidin-2-amine

Product 1

HCID 68413686N'-(2-amino-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (0.5 g, 2 96 mmol) and 2-furoic acid hydrazide (0.76 g, 6.0 mmol) are taken into 30 mL of n-butanol. The mixture is stirred at 120° C. under N2 for 2 h. The solvent is evaporated in vacuum and the residue is triturated with water and filtered to afford compound N′-(2-amino-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide: LC/MS (M+1=259.32). This material is used in the next step without further purification.

Workup

  1. customThe solvent is evaporated in vacuum
  2. customthe residue is triturated with water
  3. filtrationfiltered

Sources & evidence

ORD record
ord-c504f7736a544ef0a1f5bda51ed03146
Source dataset
uspto-grants-2010_05
Patent number
US07723343B2

Reaction notes

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